Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 99 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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Hawaii
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Superb117 reviews4.9
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Deluxe Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb440 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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Hawaii
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Superb913 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Sunset and Manta Ray Snorkel Adventure
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays! Upon arriving, receive an in... More

Sunset and Manta Ray Snorkel Adventure
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Hawaii
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Superb772 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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Hawaii
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Superb26 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Snorkel with Manta Rays Guaranteed
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Snorkel with Manta Rays Guaranteed
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Hawaii
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Superb702 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
Pau Hana Sunset Cocktail Cruise
Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Pau Hana Sunset Cocktail Cruise
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Hawaii
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Superb55 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....
Sunset Sail Experience at Kona from Honokohau
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Sunset Sail Experience at Kona from Honokohau
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Hawaii
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Superb157 reviews4.8
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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Hawaii
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Superb221 reviews4.9
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
BYOB Waikiki Sunset Swim and Diamond Head Sailing
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

BYOB Waikiki Sunset Swim and Diamond Head Sailing
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Hawaii
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Superb153 reviews5
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
Sail and Turtle Snorkeling Tour in Waikiki
Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an epic 2-hour boat adventure that combines the thrill of sailing past Diamond Head with the magic of snorkeling with turtles in their ... More

Sail and Turtle Snorkeling Tour in Waikiki
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Hawaii
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Superb247 reviews4.8
Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an ep....
Half-Day Deluxe Molokini Snorkel Excursion in Maui
Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to th... More

Half-Day Deluxe Molokini Snorkel Excursion in Maui
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Hawaii
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Superb80 reviews4.9
Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snor....
9am Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

9am Turtle Canyon Snorkel Adventure
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Hawaii
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Superb254 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Sunset Party Cruise–DJ, Trampoline, BYOB & Cocktails (18+)
This is not your average sunset cruise — it’s a party made exclusively for adults 18 and older. Our Disco Sunset Party Cruise blends the thrill of ocean adventure with vibrant party energy. You’ll kick off the evening with ... More
Free Cancellation
(Saving 20% )

Sunset Party Cruise–DJ, Trampoline, BYOB & Cocktails (18+)
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Hawaii
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Superb254 reviews4.9
This is not your average sunset cruise — it’s a party made exclusively for adults 18 and older. ....
Free Cancellation
(Saving 20% )
Hawaiian Canoe Sailing Experience in Maui
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Hawaiian Canoe Sailing Experience in Maui
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Hawaii
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Superb58 reviews4.8
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
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Hawaii
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Superb185 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
Sunset Sail from Ma'alaea Harbor
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to ex... More

Sunset Sail from Ma'alaea Harbor
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Hawaii
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Superb208 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
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Hawaii
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Superb17 reviews4.7
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....
Private Catamaran Charter in Waikiki (1-6 Guests)
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More
Private Tour

Private Catamaran Charter in Waikiki (1-6 Guests)
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Hawaii
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Superb17 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
Private Tour
Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani
Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breath... More
Private Tour

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani
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Hawaii
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Superb36 reviews4.8
Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. Th....
Private Tour